Monthly and Winter Rentals in Hilton Head, SC
Hilton Head monthly rentals, for a month or the whole winter: who offers them, and how a 90-day stay skips the 10% rental tax.
See rentals and pricesWinter Homes Priced by the Month
Skip the tax at 90 daysAll-in prices for a 28-night stay, with taxes and fees. Tap a home for the exact price for its dates.
HHI.com partner
Ocean Breeze
Villa 48
2 bed · 2 bath · Sleeps 6
November · about $3,474 for 28 nights
All fees included
Saves about $3,050
Open Nov 7 – Dec 5
HHI.com partner
Forest Gardens Villas
Villa 53
2 bed · 1 bath · Sleeps 5
November · about $3,474 for 28 nights
All fees included
Saves about $3,050
Open Nov 7 – Dec 5
HHI.com partner
Forest Gardens Villas
Villa 34
2 bed · 2 bath · Sleeps 6
November · about $3,474 for 28 nights
All fees included
Saves about $3,050
Open Nov 7 – Dec 5
HHI.com partner
Ocean Breeze
Villa 42
2 bed · 2 bath · Sleeps 6
November · about $3,477 for 28 nights
All fees included
Saves about $3,047
Open Nov 7 – Dec 5
HHI.com partner
Ocean Breeze
Villa 47
2 bed · 2 bath · Sleeps 6
November · about $3,478 for 28 nights
All fees included
Saves about $3,046
Open Nov 7 – Dec 5
Top 20 rated homes for a winter month
See all 487 winter rental homes, top rated first
Palmetto Dunes
5-bedroom home on Full Sweep, sleeps 15
5 bed · 4 bath · Sleeps 15
$593–$1,386 a night
All fees included
Forest Beach
5-bedroom home on Sandpiper Street, sleeps 10
5 bed · 5½ bath · Sleeps 10
$730–$1,622 a night
All fees included
Bradley Beach
6-bedroom home on Barrier Beach Cove, sleeps 16
6 bed · 6½ bath · Sleeps 16
$595–$1,643 a night
All fees included
HHI.com partner
Sea Pines
3-bedroom home on Tupelo Road, sleeps 8
3 bed · 2 bath · Sleeps 8
$336–$833 a night
All fees included
Forest BeachOceanfront
7-bedroom home on Roadrunner Lane, sleeps 20
7 bed · 7½ bath · Sleeps 20
$945–$3,695 a night
All fees included
Top 20 rated villas for a winter month
See all 1,008 winter rental villas, top rated first
SeaCrestOceanfront
Villa 2408
2 bed · 2 bath · Sleeps 6
$259–$759 a night
All fees included
Snowbird stays welcome
Homes and Villas Open for Two Months This Winter
1,008 villas and 487 homes from $90 a night with taxes and fees.
1495 rentals
Springwood Villas
- 2 bed
- 2½ bath
- Sleeps 6
King bed
HHI.com partner
$195–$330
a night
All fees included
The BreakersOcean view
- 1 bed
- 1 bath
- Sleeps 6
King bed
HHI.com partner
$202–$512
a night
All fees included
The BreakersOceanfront
- 1 bed
- 1 bath
- Sleeps 6
HHI.com partner
Only 1 open week left in February
$153–$391
a night
All fees included
Plantation Club Villas
- 2 bed
- 2 bath
- Sleeps 4
HHI.com partner
Only 1 open week left in February
$185–$399
a night
All fees included
Forest Gardens Villas
- 2 bed
- 2 bath
- Sleeps 6
HHI.com partner
Only 1 open week left in March
$166–$334
a night
All fees included
Plantation Club Villas
- 3 bed
- 3½ bath
- Sleeps 8
King bed
HHI.com partner
Only 2 open weeks left in May
$216–$634
a night
All fees included
Forest Beach
- 3 bed
- 2 bath
- Sleeps 8
HHI.com partner
$224–$605
a night
All fees included
Queens Grant
- 3 bed
- 2½ bath
- Sleeps 8
Pets allowed · King bed
HHI.com partner
$229–$588
a night
All fees included
Forest Beach Villas
- 3 bed
- 2 bath
- Sleeps 6
King bed
HHI.com partner
$242–$608
a night
All fees included
Not sure which rental fits?
John Alagna, CEO, HHI.comHilton Head, SC
How Hilton Head Island Long-Stay Rentals Work
Winter rentals on Hilton Head Island, SC, are the same furnished homes and villas that rent by the week in summer. From fall to spring, when weekly demand drops, companies open them to stays of a month or more at a lower monthly rate. Most name a season: Sunset Rentals rents monthly from October 1 to April 1, host2coast gives its monthly discount from October through February, and Vacation Time of HHI’s snowbird dates for 2026-27 run November 1 to March 20. A few homes rent by the month all year.
The monthly rate usually starts at 28 to 30 nights, and it is rarely shown online: most companies quote a long stay by phone. What it covers varies. Dwell’s monthly rate includes utilities, Wi-Fi and departure cleaning, while Vacation Time’s leaves out departure cleaning, taxes and fees, and bills electricity over $100 a month. Payment and cancellation terms are stricter too: Island Rentals of Hilton Head makes any booking of 28 days or more non-refundable, and Five Star Properties asks for 120 days’ notice to cancel a monthly stay. Book Hilton Head snowbird rentals early: many snowbirds rebook the same home every year, so the best homes for January and February go first.
Winter 2026-27 Monthly Rentals: Windows and Minimums
The monthly season opens in the fall. Sunset Rentals starts renting by the month on October 1, host2coast’s monthly discount runs from October, and Vacation Time of HHI’s snowbird stays begin November 1 and end March 20. The two HHI.com partners, Island Rentals and Coastal Vacations, take stays of a month or longer and quote them by phone. Most companies start the monthly rate at 28 to 30 nights.
| Company | Season | Minimum stay |
|---|---|---|
| Island Rentals of Hilton Head | No season published | A month or longer; a booking of 28 days or more is non-refundable |
| Coastal Vacations | No season published | 28 days or longer |
| Sunset Rentals | October 1 to April 1 | By the month; quotes by phone |
| Vacation Time of HHI | November 1 to March 20 | 30, 60 or 90 days |
| host2coast | October through February | More than 28 days for the monthly discount |
| Dwell Vacation Rentals | No season published | 30 nights or more |
| Coastal Home and Villa | No season published | 27 nights or more |
Windows and minimums come from each company’s own long-stay page. Many snowbirds rebook the same home year after year, so January and February go first: call early, ask for the total with every tax line, and see what to ask before you book. Companies not listed may still take a long stay; find them all in the rental company directory. Rent by the month and not listed here? Get in touch.
Stay 90 Days and Skip the 10% Tax
Rentals shorter than 90 days in a row carry 10% in taxes: 7% to South Carolina and 3% to the Town. Book 90 nights or more and neither applies, which saves about $100 on every $1,000 of rent. Ask the company to show the tax lines on your quote.
Where a Month-Long Stay Is Allowed
The resort areas that rent by the week also rent by the month. Some private, residential communities bar any lease shorter than 90 days or six months, whatever the Town allows.
Monthly Stays Allowed
Book a month or the whole winter.
Sea Pines
Homes and villas here are rented by the week and by the month; several island companies list Sea Pines homes for monthly stays, including one in Harbour Town.
Palmetto Dunes
Oceanfront villas in Palmetto Dunes turn up in several companies’ monthly and winter collections, from Windsor Place to Hampton Place.
Forest Beach
The condos and homes around Coligny and North Forest Beach are in companies’ snowbird lists, a walk or a bike ride from shops and restaurants.
Folly Field
Oceanfront villas at Sea Cloisters, on the beach at Folly Field, are in one company’s monthly collection.
Moss Creek
Just over the bridge, off the island. Rentals must run at least a month, so confirm the current minimum with the association.
90-Day Minimum
Plan on a full season, three months or more.
Sun City Hilton Head
In Bluffton, not on the island. Every lease must run at least 90 days, and tenants must meet the community’s age rule.
Six-Month Minimum
Not an option for a winter month; these suit a long-term lease.
Hilton Head Plantation
Leases must run at least six months unless the board approves otherwise, so a winter month is not an option.
Indigo Run
Every lease must run at least six months, with no subletting.
Long Cove
The covenants bar leases shorter than six consecutive months without the association’s written permission.
Windmill Harbour
Homes can’t be rented for less than six consecutive months.
Hilton Head Winter Rentals: What the Season Is Like
Winter is the island’s quiet season, not a closed one. Afternoons are mild, nights are cool, and the beaches and bike paths are yours. The ocean is too cold for most swimmers, so a winter rental is about walks, golf, bikes and long dinners rather than days in the water. Hurricane season ends on November 30. Here are the averages for a snowbird season; the Hilton Head weather guide has every month.
| Month | Average high | Average low | Rain | Ocean |
|---|---|---|---|---|
| November | 70°F | 49°F | 2.6 in | 66°F |
| December | 63°F | 43°F | 3.1 in | 58°F |
| January | 60°F | 40°F | 3.4 in | 53°F |
| February | 63°F | 42°F | 3.2 in | 56°F |
| March | 69°F | 48°F | 3.9 in | 62°F |
Dogs get the beach to themselves too: from Oct 1 to Mar 31, the Town allows them on the sand at any hour, on a leash or under voice control (see the dog-friendly beaches guide, and the dog-friendly rentals page for homes that take them). It is oyster season, with the island’s seafood markets at their best, and Shelter Cove Harbour marks the holidays with A Coastal Christmas.
Before You Book a Hilton Head Snowbird Rental
The monthly rate, in writing
Most companies quote long stays by phone. Ask for the total for your dates, with cleaning, fees and every tax line.
Utilities
Some include them and some cap them: one company charges for electricity over $100 a month. Ask what the rate covers.
Cancellation terms
Long stays often have stricter rules, from non-refundable bookings to a 120-day cancellation window. Price in travel insurance.
Cleaning and linens
A weekly rental is cleaned once, at the end. For a month or more, ask whether a mid-stay clean or linen change is included or extra.
A heated pool
Many complex and private pools are seasonal, and some homes heat theirs only for a fee. Ask what is open in the months you are there.
Pets and the pass
Check the home’s pet rule, and in a gated community ask how a long-stay guest gets a gate pass for the whole stay.
Staying Six Months or Longer?
Past a season, you are looking for a lease, not a vacation rental: an unfurnished or furnished home for six or twelve months, through a long-term rental company. That side of the market, including the communities that only allow six-month leases, is on the Hilton Head long-term rentals page.
Frequently Asked Questions
Updated
Can you rent a vacation home on Hilton Head by the month?
Yes. Many island rental companies rent homes and villas by the month, mostly from fall through early spring. Sunset Rentals, for one, rents monthly from October 1 to April 1, and Vacation Time of HHI rents snowbird stays of 30, 60 or 90 days from November 1 to March 20 for the 2026-27 winter.
How many nights count as a monthly rental?
It depends on the company. Dwell gives its monthly rate on any stay of 30 nights or more, Coastal Vacation Rentals and host2coast start at 28 days, and Coastal Home and Villa treats 27 nights or more as a long stay.
Do you pay tax on a monthly rental in Hilton Head?
Yes, if the stay is shorter than 90 days in a row. South Carolina charges 7% (5% sales tax and 2% accommodations tax) and the Town of Hilton Head Island adds 3% (a 1% accommodations tax and a 2% beach preservation fee). A stay of 90 consecutive days or more is outside both.
Is a monthly rental a short-term rental under the Town’s rules?
No. The Town’s short-term rental ordinance defines short-term as less than 30 days, and it covers condos, villas and houses. It does not apply to timeshares or hotels.
Which Hilton Head communities don’t allow monthly rentals?
Hilton Head Plantation, Indigo Run, Long Cove and Windmill Harbour require leases of at least six months, and off the island Sun City Hilton Head requires 90 days. Moss Creek, just over the bridge, allows rentals of a month or more.
What is the weather like on Hilton Head in the winter?
Mild. January, the coolest month, averages highs near 60°F and lows near 40°F, and the ocean is in the low 50s, so the beach is for walks rather than swims. By March, afternoons average about 69.
Can I bring a dog on the beach in the winter?
Yes. From October 1 to March 31 the Town allows dogs on the beach at any hour, on a leash or under voice control. The rental home sets its own pet rule.
More Ways to Plan a Long Stay
Hilton Head vacation rentals: beach houses, condos and villas by beach area and complex, who manages them, dog-friendly homes, and how renting works.
Hilton Head rental companies grouped by what each rents, from resort programs to Sea Pines specialists, with phone numbers and links to each one.
Pet-friendly rentals in Hilton Head: which communities and complexes allow dogs, the beach leash rules by season, and companies with pet filters.
Hilton Head long term rentals: houses, villas and condos for rent by the year, the local companies that rent them, and what to ask before you sign.
Hilton Head weather by month: average highs, lows, rainfall and ocean temperature for all 12 months, plus hurricane season and the best time to visit.
Every Hilton Head beach is dog-friendly, but leash rules change by season and hour — plus a no-dog zone near Fish Haul Creek. Here’s exactly when and where.
Keep exploring
Harbourwood Villas in Sea Pines: single-story two-bedroom villas on the 9th hole of Harbour Town Golf Links. Who rents them and how to book.
Muirfield Villas in Sea Pines: three- and four-bedroom villas on Harbour Town Golf Links with golf and lagoon views. Who rents them.
Hilton Head Guest Services sells discounted activities and getaways, but the best prices need a 90-minute Palmera timeshare tour. What to ask first.
Hilton Head oceanfront rentals: which villa and condo complexes sit on the beach, which are a row back, and the island companies that rent them.
Your beach week starts here
Compare villa and beach home prices from local rental companies side by side, and catch last-minute deals before they’re gone.
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